Islesboro Vacation Packages

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Your Islesboro Vacation

When you organize a vacation package to Islesboro, you can relax and enjoy your getaway knowing your travel plans are in order. Discover the many charms of this amazing city from your base in a neighborhood like Bayside, which is great for history. If sightseeing is on the agenda during your trip to Islesboro, stop by major attractions like Windsor Chairmakers, Schoolhouse Museum and Warren Island State Park. A few quick clicks is all it takes to build your ideal Islesboro vacation on Expedia.

Top Islesboro Vacation Deals

Price found within the past 48 hours. Click for updated prices.
Harborline Hotel

Harborline Hotel

3 out of 5
per person
Jun. 11 - Jun. 16
found 24 hours ago
Roundtrip non-stop flight included
Montreal (YUL) to Rockland (RKD)
7.6/10 Good! (921 reviews)
The room was super clean. The bathroom was newly remodeled. The front staff was very friendly and helpful! This was a great stay for a hotel in our budget. The view of the water (yes, across the parking lot) was fantastic. Got to watch the ferry come in! Would stay here again in a heartbeat!

Reviewed on Apr. 20, 2025

Country Inn at The Mall

Country Inn at The Mall

2 out of 5
per person
Jun. 11 - Jun. 16
found 24 hours ago
Roundtrip non-stop flight included
Montreal (YUL) to Bangor (BGR)
9.4/10 Exceptional! (2,320 reviews)
Very nice and clean.

Reviewed on Apr. 29, 2025

Hollywood Casino Bangor

Hollywood Casino Bangor

3 out of 5
per person
Jun. 11 - Jun. 16
found 24 hours ago
Roundtrip non-stop flight included
Montreal (YUL) to Bangor (BGR)
8.6/10 Excellent! (1,091 reviews)
Loved the 2 restaurants, great casino

Reviewed on Apr. 29, 2025

Belfast Harbor Inn

Belfast Harbor Inn

3.5 out of 5
per person
Jun. 11 - Jun. 16
found 24 hours ago
Roundtrip non-stop flight included
Montreal (YUL) to Bangor (BGR)
9.6/10 Exceptional! (1,002 reviews)
Across the river from downtown, but a quick drive. Awesome motel, decent breakfast, nice view from the balcony.

Reviewed on Apr. 29, 2025

Comfort Inn

Comfort Inn

2.5 out of 5
per person
Jun. 11 - Jun. 16
found 24 hours ago
Roundtrip non-stop flight included
Montreal (YUL) to Bangor (BGR)
9.2/10 Wonderful! (1,004 reviews)
Hotel is very clean. Conveniently located off highway and big shopping mall within walking distance. Lots of dining options within walking distance. Fresh baked cookies daily. Friendly staff.

Reviewed on Apr. 20, 2025

Ready to book your vacation to Islesboro?

 

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Islesboro Hotel Deals

Island log home in Maine with ocean views
Island log home in Maine with ocean views
Islesboro
Cozy cabin
"Cozy, quiet cabin with a good layout and nice view on the water. Easy check-in and check-out process. Host is very responsive."

Reviewed on Jan. 8, 2025

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Island log home in Maine with ocean views
The Country Inn at Camden Rockport
The Country Inn at Camden Rockport
2.5 out of 5
8 Country Inn Way, Rockport, ME
Fully refundableReserve now, pay when you stay
The price is CA $178 per night from May 4 to May 5
CA $178
CA $194 total
includes taxes & fees
May 4 - May 5
9.4/10 Exceptional! (1,001 reviews)
"Pleasant staff. Large spacious room. Nice view out the window."

Reviewed on Apr. 27, 2025

The Country Inn at Camden Rockport
Fireside Inn & Suites - Belfast
Fireside Inn & Suites - Belfast
3 out of 5
159 Searsport Avenue, Belfast, ME
Fully refundableReserve now, pay when you stay
The price is CA $209 per night from May 13 to May 14
CA $209
CA $228 total
includes taxes & fees
May 13 - May 14
8.6/10 Excellent! (782 reviews)
Room choices
"Would like a 2 bedroom with a living room"

Reviewed on Apr. 19, 2025

Fireside Inn & Suites - Belfast
See all 1,304 properties in Islesboro
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

All Inclusive Vacations

All Inclusive Vacations

Beach Vacations

Beach Vacations

Family Vacations

Family Vacations

Frequently asked questions

How much does an Islesboro vacation package cost?
Offering great value package deals from CA $718 on Expedia, you’ll be thrilled with how little a vacation to Islesboro costs! Expedia’s packages make travel planning easier and save you more.
What are the cheapest months to go to Islesboro?
Plan your trip for the low or shoulder season and you’re likely to find cheap Islesboro vacation packages. Keep in mind that school vacation periods and local events and festivals can have an impact on prices, so do your research before you go.
How many days is enough for Islesboro?
The ideal duration of your Islesboro vacation depends on what you’d like to do and see. Typically, a handful of days to a week will give you enough time to visit all the main attractions and discover some hidden gems along the way.
How to find the best Islesboro package deals?
Use Expedia’s filters to help you find some of the best Islesboro package deals. When you begin your search, simply set your maximum budget and then order the results by “Price: low to high.” If you want to save, plan your adventure for midweek, or browse for Islesboro package deals in the off-peak season. Play around with your travel dates and you may land even better discounts. As a rule of thumb, it’s usually best to lock in your vacation package as soon as possible.
Is it cheaper to book an Islesboro vacation as a package?
An Expedia vacation package could land you great savings when compared to booking flights and hotels separately. Better still, you can customize your Islesboro getaway to match your exact style. Choose your preferred flight time, select the hotel type and add a rental car. Browse our great deals to see how much you can save.
When to book a vacation package to Islesboro?
If you have your Islesboro vacation dates locked in, book early to bag some unbeatable deals. With Expedia, you can often reserve some flights up to one year in advance. Prefer spontaneous getaways? Our last-minute deals are great for impromptu escapes.
How to plan a trip to Islesboro?

  1. Choose the best time to travel: Your schedule, preferred season and the type of weather you like can all influence your decision on when to travel to Islesboro.
  2. Work out your budget: Make sure you have enough money to pay for everything from transportation and dining out to airfares and activities. Your hotel will likely be the biggest expense during your trip to Islesboro.
  3. Decide your trip length: Consider how much time you’d like to spend discovering Islesboro. Plan your itinerary so you can get to all the attractions and experiences you’re interested in without rushing.
  4. Combine your flights and hotel: Awesome destination, check. Length of stay, check. All that’s left now is to pick an Islesboro vacation package that brings all your bookings together.

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.